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Cheap flights from Boston (BOS) to Chicago (CHI)

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1 Adults (11+)
0 Children (2~11)
0 Infants (0~2)
Save up to 31%
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
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Cheap flights from Boston to Chicago in June , July 2026

30 Jun - 14 Jul $ 149.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
Pick dates
13 Jun - 08 Jul $ 234.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
1 STOPS
BOS
Boston
Pick dates
13 Jun - 01 Jul $ 282.00
BOS
Boston
JetBlue Airways
DIRECT
CHI
Chicago
CHI
Chicago
JetBlue Airways
DIRECT
BOS
Boston
Pick dates

Last minute flights from Boston to Chicago

23 Jun - 30 Jun $ 170.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
Pick dates
19 Jun - 30 Jun $ 208.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
Pick dates
16 Jun - 30 Jun $ 309.00
BOS
Boston
United Airlines
DIRECT
CHI
Chicago
CHI
Chicago
United Airlines
DIRECT
BOS
Boston
Pick dates

One-way flights to Chicago from Boston

10:35 AM - 10:35 AM
United Airlines
0 Stops
2h 53m
BOS - CHI
$ 96
Kiwi
Pick dates
3:08 PM - 3:08 PM
United Airlines
0 Stops
2h 52m
BOS - CHI
$ 134
Kiwi
Pick dates
3:08 PM - 3:08 PM
United Airlines
0 Stops
2h 52m
BOS - CHI
$ 134
Kiwi
Pick dates

How to find the cheapest flight from Boston (BOS) to Chicago (CHI)

Related info for your journey
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How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.
How to find the cheapest flight from Boston (BOS) to Chicago (CHI)
Some placeholder content for the first accordion panel. This panel is shown by default, thanks to the .show class.